Tetrahydrofuran → [2-(2,6-Dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of [2-(2,6-dichloro-benzyl)-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine (110 mg, 0.22 mmol) in THF (6 mL) and MeOH (6 mL) was added a solution of potassium peroxymonosulfate (406 mg, 0.66 mmol) in H2O (6 mL). The resulting mixture was stirred vigorously at 40° C. After 24 h, the mixture was concentrated and the crude residue was diluted with satd. aq. NaHCO3 (10 mL) and extracted with EtOAc (10 mL×3). The combined organic layers were dried, concentrated, and purified by FCC to afford a colorless solid (100 mg, 85%). MS (ESI): mass calcd. for C20H13Cl2F3N4O2S2, 531.9; m/z found, 532.9 [M+H]+. 1H NMR ((CD3)2SO): 11.02 (s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.77 (d, J=8.7 Hz, 2H), 7.64 (d, J=8.1 Hz, 2H), 7.50 (dd, J=8.5, 7.8 Hz, 1H), 4.89 (s, 2H), 3.37 (s, 3H).

Provenance & Evidence